Subject: Square Appointments Waitlist — Delayed Availability Notifications for Already-Open Appointment Times
I’m reporting what appears to be a problem with the automated waitlist notifications in Square Appointments.
I tested the waitlist myself because I noticed a customer sitting on our waitlist even though appointment times matching his requested availability were already open on our calendar.
To test the behavior, I went through our public Square booking site as a customer.
Test performed:
On Saturday, August 22, 2026 at approximately 2:56 PM, I selected Tailored Haircut with Dave and viewed availability.
Square’s booking page showed:
“No availability until Monday, August 24.”
Monday, August 24 therefore already had appointment availability in the booking system.
Instead of selecting the available Monday appointment, I chose Join the waitlist and entered:
Date: August 24, 2026
Time: Any time
Square accepted the waitlist request and displayed:
“You’re on the waitlist, David! We’ll let you know if a spot opens up!”
At 2:56 PM Saturday, I immediately received the confirmation text stating that I had successfully been added to the waitlist.
However, I received no notification informing me about the appointment availability that already existed for Monday.
Then, at 7:29 AM on Monday, August 24, Square sent:
“The appointment you requested at The Urban Shave Barber Shop may now be available on Monday, August 24, 2026. Act fast to book an appointment…”
The issue is that this availability was not new. Appointment times on August 24 were already available when I joined the waitlist approximately 40 hours earlier.
Nothing needed to “open up.”
This creates a significant problem for us as a business. A customer can join the waitlist while an appointment matching their request is already available, reasonably believe they need to wait for Square to notify them, and then not receive that notification until much later. Meanwhile, a bookable appointment can remain unfilled.
Please have the Appointments technical team review this specific waitlist request and determine:
- What event triggered the availability notification at 7:29 AM on August 24?
- Why did the system not recognize and notify me of the existing August 24 availability when I joined the waitlist on August 22?
- Are waitlist openings evaluated in real time, periodically, or only when certain calendar events occur?
- Is the approximately 40-hour delay expected behavior or a defect?
- If this is expected behavior, please explain exactly how automated waitlist matching and notification timing currently work.
I have timestamped screenshots documenting the booking availability, waitlist request, confirmation, and delayed availability notification and can provide all of them.
Because we are paying for Square’s appointment and business services, we rely on the automated waitlist specifically to help fill otherwise-unused appointment time. A delay of this nature defeats much of the business purpose of the feature.
Please escalate this beyond general troubleshooting if necessary. I’m specifically requesting that the waitlist event and notification logs for this test be reviewed so we can determine why the notification was generated when it was.
Thank you,
Dave
The Urban Shave Barber Shop
